How to Plan a Vacation

It seems counter intuitive, but I’ve read that at the end of August is one of the best times to plan a vacation because you can get the best deals. We’ve talked about how to deal with vacation stress (including how to be a good employee while on vacation, and a vacation time poll to gauge how much you’ve actually taken) and we’ve talked about office etiquette around the holidays — but we haven’t talked about planning a vacation in a long time, so I thought we could discuss. How do you budget for a vacation, both in terms of money and time? (Does anyone do the “extra savings account just for vacations” thing?) Do you like to vacation in the summer or some other time of the year? Have you taken the same vacation multiple times (for example, I’ve been on FOUR Paris vacations — I love the city and love seeing new sides to it every time I go)? Or are vacations all about family for you, spending time with your parents (either in your childhood home or at a family beach house or the like)?

For my $.02, I’ve never been very good at planning vacations, which is probably one of the reasons I prefer staycations. When I was working in Big Law (and was single) I didn’t want to plan big vacations for myself because a) I never knew when work would be crazy and b) I didn’t particularly want to travel by myself (I’ve done it and have liked it, but I just generally would prefer to travel with someone else). Then when I moved to a smaller job, even though I was married by then, I went from 4 weeks to 2 weeks of vacation time — which pretty much meant all of that went to holiday visits with my Ohio family. Now that I’m self-employed (and we have a toddler who goes to bed at 7:30 and takes a long nap in the middle of the day), going to a new city or space seems hardly relaxing, primarily because of his schedule (to say nothing of the need for stringent babyproofing and the stress of trying to prepare a week’s worth of blog content ahead of time!). So tell me how it’s done, ladies — how have you made time for vacations throughout your life?

(Pictured: me on vacation in Germany (in front of the Linderhof Castle) in, um, 2005. Why yes, those are pigtails.)

Comments

Planning vacations just makes me stressed. My boyfriend and I vacationed to the Florida Keys because I’ve been there several times and it’s easy to fill 4-5 days without having a set schedule.

Lately I’ve been getting the itch to go somewhere else (San Fran, Austin/San Antonio, Boston) but I’m overwhelmed about planning it. I’m sure I could figure it out. The other thing is I need to request time off far in advance.

I have a decent amount of Southwest/Marriott points because I travel for work, so that brings the cost down a good amount. I don’t see myself traveling forever, but if I leave this place, having to pay full price for a vacation would definitely be a downer.

I think it’s helpful to distinguish between 1) Vacations; 2) Traveling; and 3) Seeing Family. Sometimes these things coincide, but often they don’t, and I am always happier when I have a clear sense of what the expectation is. So for me, a week at a beach resort is vacation; a sightseeing tour of Italy is Traveling (plus vacation); and a week in my hometown is definitely Seeing Family. Now that I have two kids, we no longer Travel, but we do See Family, and I am trying to add in some Vacation to our mix.

In some ways, being on the school schedule helps with all of this. I don’t have childcare for the weeks when my preschooler’s school is on break, so I have to take time off work or arrange childcare for those weeks and I might as well book a vacation at the same time.

I like this break down of Vacation vs. Travel Vs. Visiting family. An ex-BF and I got in a large argument while traveling in Italy, because I considered it a sightseeing trip and he considered it a vacation.

I’m single and enjoy carefully planning my vacation days for a mix of all three types of travel. Ideally I can mix a little as well. For example, over this weekend I am going on vacation with my siblings and thier SOs.

I like this breakdown. I’m married, no kids yet. We alternate between Vacations and Traveling for our “just the two of us” trip each year, with one or two other weekends away, and prioritize this time over other travel — I’m in Biglaw and if I can only take one solid vacation a year, you’d better believe I’m not using it for an extended family trip. (My in-laws live further away, and we’ve convinced them to visit us so they see us more often – works great!)

This is a great breakdown and so true. I’m generally not someone who Vacations unless the Vacation is combined with Travel. Seeing Family is usually a completely separate item.

One of the great joys of my life is planning Travel. I prefer to travel during the “dark” times of the year – February/March is a favourite for me, as well as October/November. The airfares are usually cheaper and destinations are far less crowded. However, since setting up house with my SO, I’ve had to adjust – it is difficult for him to take time off other than at Christmas and at the end of July.

When I was on my own, I informally saved up for trips and was pretty lenient about putting airfare on my credit card. However, now that I’m planning trips for two, I’m trying to be far more responsible about saving the money in advance. This has cut down on the frequency of my trips, which saddens me, but I know I’m being far more responsible.

The next big trip that my SO and I are planning will be in the spring, with a 4 or 5 month old baby – we are going to Bangkok and Singapore, both of which I’m familiar with but my SO has never visited. I’m looking forward to showing him around but it will be a fun challenge with a baby! The trip will look a lot different than what we would do on our own, but I still think it’s worthwhile. I also wanted to go to London on my own this fall but am going to do the financially responsible thing and abstain, much as it pains me…

Seeing Family usually happens on weekends, since my family is only a few hours away. We’re lucky that we don’t have to plan long trips to do that, and it usually doesn’t require days off.

Also like the breakdown categories.
Nonny… hmm… I have a 15-mo old and a trip like that sounds like a nightmare. I’ve been to Thai/Sing… meh, going to a local cabin or cottage with my tot is hard enough. More power to you if you can enjoy it- you can do it, yes, whether it’ll be worth the hassle is the question- not for me- I’d be wayyyy to exhausted. Just taking her on cross-coutry flights at 5mo was miserable. I’ve put off Travel except when she isn’t in tow for now in favor of Vacations regionally.

Love this break-down, and agree that those are three separate things! However, they can be blended. Last year we combined a ‘vacation’ with ‘seeing family’, as we all chipped in and rented a big beach house for a week in my home state, where my parents and sister still live. It was a great way to blend the two types of trips, and we all were more relaxed for it!

Definitely loving this breakdown. We’re lucky enough to be nearby to most family (<1hr), but arranging travel to visit my sister (who is at the other end of the country) has caused a bit of contention – spouse has no interest in visiting, but I think it's unfair to put it on her to have to travel to see us all the time, especially since we can afford it much more readily than she can. So that kind of falls under all 3 categories, since we try to build in some cool stuff while we're there (like visiting the local Aquarium).

That aside, we don't do a lot of Traveling these days – with 2 small kids, we usually need a Vacation with lots of downtime instead.

I'm not a big fan of the staycation – I end up just feeling slummy because I should be doing something productive. Going away forces me out of the usual mindset. That's not to say that going away doesn't have its own stresses, but it's a break.

As for planning, if we have a specific destination in mind, I'll usually do research on my lunchhours and book online. If we only have vague goals (like "somewhere warm, with babysitting, for these dates") then I'll usually talk to my travel agent (started with one specific trip that had good results, so now I go back to the same guy each time). It's about as time consuming to talk to the agent for something random as to book something where I already know most of what I want, but when I'm going somewhere I haven't been before I like having a baseline recommendation and I don't have the time to do tons of legwork.

Workwise, I typically don't have a problem being able to book something, but I almost always end up paying for it by having to catch up on everything I missed – usually takes about a month to clear everything off. I also have a personal policy of "If I'm on vacation, I'm not checking email or phone" but I do make arrangements for other people to cover urgent issues. Spouse, on the other hand, does have to check in for urgent stuff, but that's usually manageable in half an hour a day, which is pretty reasonable (and which is officially part of his job description, so we accept it as a necessity and work it in to the plans).

I don’t differentiate between Traveling and Vacation, because ideally we do some relaxing and some sightseeing, etc. on “vacation”. However I do agree that seeing family/going to family events (weddings, reunions, graduations, etc.) is not a vacation. My husband grew up in a family that only ever went anywhere for family events and was confused that we traveled to places where we had no family, just for fun. He now agrees he likes these trips, haha, but my MIL still gets frustrated with us that we do not go to every single event in his very large family, because we want to travel outside of those as well.

I can totally understand the three categories and the need to understand expectations about time off. It has been a source of disagreement between me and DH. To him anytime he is not in work is a vacation, so when we go and visit his mother, that’s seeing family and a vacation. To me it’s seeing family, and not something I want to spend a whole week doing when she can fly up to see us. I would rather either save the paid time off for (hopefully) a future maternity leave, travel, or an actual (to me) vacation.

That’s an interesting perspective! I do distinguish between Travel and See Family, but I’ve never considered Vacation a separate category. As I think about it, I feel completely rejuvenated by Travel, so I’ve not needed to plan a Vacation separately. When I’m feeling a little stressed out by work and need to click off mentally, I turn to hobbies or road trips.

I don’t budget for travel in a separate account. I usually just build in a cushion for it in my Mint budget, and ‘accrue’ for it all year. When I do go on vacation, I put all the costs on a points-earning credit card and pay it off in a month or two. I need at least two weeks for a trip to be considered a proper Travel/Vacation and I generally prefer to go abroad, so two weeks becomes necessary. Usually take it in the shoulder season – March-April and August-Sept.

I personally divide travel between ‘Family Holiday’ and ‘Parents Only Holiday’. Luckily family is all within a 3 hr drive and easy to do on a weekend, so we just include the gas & meals for the drive in our regular budget – we don’t need hotels or anything like that.

Our Family & Parents Only holidays generally are active holidays (especially Disney back in April). If we are doing something relaxing it’s usually just the 2 of us, but even then I’m not one that can sit for hours on a beach. I like to go & do things. Dh is a sit on the beach kind of guy, so when we go places just the 2 of us, or even as a family, I try to dial back my desire to go do things, and he tolerates outings & activities so we both can be satisfied with the holiday.

We try to take one weeklong international vacation just me and my husband. I’m in Biglaw so officially have plenty of vacation time but using it can be tricky. I have a long list of places I want to go but we also use the book 1000 Places to See Before You Die and friends’ vacations as inspiration. Financially, we don’t set a specific budget but are generally pretty frugal for our income level, aiming to stay in hotels that are around $200 a night. So the biggest expense for this trip is normally the plane tickets, which are usually $1000-$2000 each. These vacations have all been in the summer so far, but this will change at some point (we really want to do New Zealand soon and not in the dead of their winter).

Then we take several long weekends to visit destinations closer to home (California) like national parks and cities that are vacation destinations. These are often on holiday weekends, which can be annoying with the crowds but us a little easier work-wise (and we always stay in cheap hotels that have free wifi so I can work). We travel with/to my parents about once a year, usually the week between Christmas and New Years. We are not Christian but work is normally light at this time, making it easier to get away. The last few years we’ve visited them, they’ve visited us, and we’ve all traveled to Hawaii together.

This.
Minimalist Planning for Travel:
(1) pick a country that we have never been to and is not under civil unrest that year (preferably alternating continents each year),
(2) spend 3-4 hours researching top activities with travel websites or with travel guides at a bookstore to get an idea about cities to visit and how many days to spend where,
(3) buy plane tickets,
(4) buy the best travel guide,
(5) reserve hotel for first and last nights,
(6) pack one carry-on only with 3-4 shirts, one sweater, one nice outfit, bathing suit, umbrella, toiletries,
(7) board plane wearing jeans, only pair of shoes, and sweater or jacket,
(8) read travel guide during the flight to plan the first few days,
(9) plan the next days on trains or at coffee shops in the country.

We are pretty frugal (used to backpack) but our income allows us to splurge if we feel like it (or can’t find a cheaper hotel/restaurant/etc), so we choose not to worry about the day to day. Hotels are important the first and last nights to avoid stress related to jetlag and getting to the airport, but we can figure out the rest once we are there. Maybe we’ll miss one or two minor sites due to our in-trip planning, but we avoid many hours of pre-trip stress.

Love Mama of 2’s categories; the failure to distinguish between a vacation and traveling definitely has been the source of some conflict in my household.

I’ve got no specific comments on this topic, but this seems like a great place to thank all of those who weighed in on my questions about a recent trip to NYC (several months ago about a place to stay and a few weeks ago about non-leather walking shoes). We had a great time — even though what I really wanted was a restful vacation, not busy traveling — in large part thanks to all of you.

We ended up renting an apt. near Union Square, which was perfect for easy travel to almost anywhere on the subway and for walking to Greenwich Village. Whole Foods was less than two blocks away, and the Strand bookstore was across the street, we could not have been better situated.

For shoes, I went with the crocs ballet flats, which were perfect to wear with dresses and long shorts and even were presentable to wear with night-out clothes until I could change shoes on arrival at a theater or restaurant. (The first day we were in town, I saw a very put-together woman of about 60 in business clothes wearing the same crocs, presumably as commuter shoes, and she looked great.) I alternated them with J-41 platform sandals — and of course red patent sling-backs when I didn’t have to walk more than a few blocks at a time.

And thanks also for all the vegetarian/vegan restaurant recs. We had great meals at Blossom, Café Blossom and Wild Ginger, good but absurdly expensive desserts at Candle 79 and post-theater cheap falafel at Maoz. We didn’t spend much time in the East Village so missed some of Funkybroad’s recommended places (and were very sad that Lulu’s Apothecary was closed when we wanted to go there), but now we have a reason to go back.

The concept of staycations depresses me. I know they have their benefits, it’s just that I hate the idea of missing an opportunity to go somewhere new when I have time off from work. There’s a wide world out there! I really enjoy planning trips, almost as much as I enjoy taking them. That said, I now have an 8-month old and traveling somewhere unfamiliar seems a lot more daunting. Mm husband and I are committed to taking the baby places when he’s young, so that he doesn’t hate spending time away from home when he’s older. But who knows, maybe we are being unrealistic about it.

Also agreed. With that said, I just took my first staycation, and it was pretty pleasant–I just moved back to a great place for grad school, but have been so busy with class I haven’t gotten to enjoy much of what makes my area awesome. So I did some of those things during my staycation, which was nice. But at the same time, I would pull my hair out if I did too many staycations. The world is just full of so many different places, why would I want to always stay in the same one?

I feel like this also but sometimes feel like things are so insane and sometimes going away for a long weekend or a week-long trip is not relaxing at all. Things have piled up at work and my trip has been busy and I come back even more stressed. I think I need a staycation or something just to get a breather (or a staycation after a vacation…)

I would have agreed with you 100% before I started working but now I understand the appeal if you have a very intense job. Very active vacations can be tiring and sometimes you feel like you need a vacation from the vacation. I have yet to do a real staycation but I have found that I now really enjoy vacations where the primary purpose is lying on the beach much more than I did previously (also destinations like Vegas that I’ve been to several times so there is no pressure to see anything and I feel no guilt about just eating and lying by the pool). There is still so much of the world to see and so I try to plan some vacations to see stuff but every once in awhile I need a vacation that is totally about relaxation. I’ve started sort of alternating very “go go go see all the sights” trips with trips where the primary purpose is staying in one place and just going to the beach/snorkeling/eating/lying around for our big vacations.

Combine an intense job with kids and staycations become even more attractive. I wouldn’t have found staycations appealing in my younger years but now spending a few days locally with my immediate family is great. And a day at home alone, spent watching mindless tv and cleaning out my (literal) closet or organizing my home office? Priceless.

Kat, you look great! As for the OP, personaly, b/c of my casekload, much of my vacations in the last 2 year’s are really only “not go physically into work” but stay very close to my MacBook Air all day, where I do all the same work from home. I was hopeing that I would be able to get a new lawyer hired who could assist me, and the manageing partner has been talkeing about it, but so far, he has YET to put an add in the NY Law JOURNAL for a new WC associate.

The manageing partner know’s that I am of the age that I need to have children, so he has been thinking of contingency plans, b/c I will HAVE to take off at least 6 week’s before and after I have children, once I get married, that is.

I found out that Sam called the manageing partner today and asked if he could come meet him. He did not clear this with me first, so I am a littel ticked off that I was bind sided by him. Sam says he is trying to feel out the manageing partner about potential business, but I think he should have come through me FIRST. What does the hive think about a potential boyfreind / spouse that does this to his girlfreind / fiiacee? I did NOT know where to look when the manageing partner came and told me that my freind, Sam, called about a meeting with him. OMG, the more I think about it, the more I am annoyed at Sam. FOOEY!

I think you have reason to be pissed. I wonder if your dad put him up to do this. If he did I would drop his saggy British Arse, buggers and all, and find a US citizen who will treat you as an equal. What a total schmuck!

I love a staycation! Or really, I love a nearcation. DH and I recently spent 5 days in a small river town an hour and a half away from our city and it was great! We went boating, went to restaurants, explored the wilderness, etc. It was very relaxing to not have to actually worry about traveling (just pack the car and go). Plus, I learned a lot about an area that was not actually far from me. For example, there were tons of house on really high stilts. I had never seen houses like that and I certainly didn’t know they were so close. And there were insane, large fish that kept leaping out the water at us and almost got in our boat a few times. Okay, now I’m just reminiscing but you get the point. The wide world includes stuff nearby.

Side note, your baby could be just as thrilled at an extended relative’s house while you go spelunking, even that’s possible for your family.

We have a separate subsection in our savings account where we put money aside monthly that funds all of these categories. We currently do a lot of weekend trips that are either “traveling” or “seeing family/friends” but are planning our first vacation since getting married two years ago. We’re going to go to San Francisco and Napa. I can’t wait!

Work: First, I swear the vacation buffer day thing is key (http://travelmoreroads.com/vacationbufferday/). See the Scientific American article in there too, very interesting. Pay attention to when other people are traveling. For example, if you think lots of people will take 4th of July week off in your office, take the same week so no one misses you, the following week so no one is around when you’re trying to wrap up and get out of the office, or the previous week so it’s quiet when you get back. I may take the Tuesday after Labor Day off actually – I’ll get four days off and probably no one will be looking for me during three of them.

$$: I do budget for vacations and estimate costs (my worksheet: http://travelmoreroads.com/resources/travel-budget-worksheet-editable-spreadsheet/). Planning helps you look forward to a vacation and makes it feel less chaotic. I do have a savings account for travel $.

Packing: Another key peace-of-mind tip. Have a packing list (here is ours: http://travelmoreroads.com/resources/packing-list/) but make it easy – just write down what you use as you get ready for work and ready for bed. There’s your toiletry kit packing list without much time added to your day. Keep your packing list from your last trip, don’t waste time repeating that process. Keep a list of things you do before you leave (e.g., turn off A/C, turn on alarm) and you’ll have a checklist for the next time.

Places/People: I like to do a mix of repeat places and new places. New places are exciting but repeat places are more relaxing because you don’t feel pressured to do and see everything and you know what to expect. I also try to do a mix of traveling with/to visit people and trips just w/ my hubby. Important to manage your expectations. Vacations are not necessarily relaxing, depends.

Thanks! Glad to be of help. :-) CNN actually loved that one too, works well for me.

By the way all, there are vacation comments in an Above the Law post today too, including how people don’t always respect out of office messages. I’m in the no email on vacation club though (gasp!), I don’t relax otherwise. Observing friends in the medical field has helped me more realistically define “emergency” situations that justify vacation interruption.

It took me years of international traveling to realize I really did need a buffer day! I’d go back to work the next day after flying home & just be scatterbrained & useless. I started adding a buffer day or two, & now I can adjust to jet-lag some at home, catch up on house chores & laundry, & will be back at work in a much clearly mindset.

The buffer day was a crazy concept to me (usually of the type fo fly out right after work and return on the red eye to go straight to work) but it is so essential to my hubby’s happiness on vacation, that I have started to build it in.

Agreed, it’s better to take a day, and go back refreshed than go back asap and be dragging for days, I like to cut my losses, so to speak. Plus the pre and post vacation craziness can undo the stress reducing effects of vacation otherwise.

Looking for opinions on how to deal with a situation with my mom (well, both my parents, but she is the more opinionated and also more easily offended of the two):

My parents will be in town this weekend cleaning out some things from my (not-so-recently deceased, long story) grandmother’s house and have asked to stay with DH and I, and have also asked that we help them move some larger heavier items. Not normally an issue, but we also just purchased a house and are not even unpacked. In addition, our house is now a 45 min drive from grandmother’s place – so it’s really only borderline convenient for them to stay with us as opposed to driving from their house (2.5 hrs away) vs doing the whole thing in one day. And that gives us a 1.5 hr round trip drive as well just to go down for the day and help them at grandmother’s.

But, since they are my parents we agreed. Now however, my mom has sprung it on me that she wants to bring her dog for the weekend, because her preferred dog sitter is not available. I like her dog in theory, but the dog is large and rambunctious, and we have a cat. Previously we have separated the two by keeping the cat outside or in the basement while the dog was here. However, as I mentioned we just moved in, just had the floors redone and still aren’t unpacked. I’m basically envisioning the dog nicking the floors with its nails and knocking over boxes of china. However, we can’t put it in the basement with the cat, for obvious reasons.

I’m tempted to ask her to find a different dog sitter, but I know she’ll be offended that I don’t want the dog at my house. Can anyone think of a different solution? Or should I just suck it up and dog-proof the house as best as possible and hold my tongue?

Does your mom frequently ask you to do things you can’t say no to? Do you have the kind of relationship where she would ask you to get a cat sitter if you were visiting her and couldn’t leave the cat at home, or would she go along with your inconvenient plan because you asked it of her?

You’re already putting off unpacking while she’s there to help move heavy furniture when you just moved into a new place (so stressful! and exhausting!). I think you can cry “New floors!” and she’ll probably understand.

I say tell her you’re not comfortable having the dog in an un dog proofed new house but that you’re happy to instead make a long day of it and do it in one day if they don’t want to leave the dog for the weekend. If she complains just repeat your boundary, don’t engage in an argument about whether it is valid.

Agreed. My mom just did the same thing to me a few months ago. If your mom is as hard headed as mine though, she might just show up with the dog anyway. Check in with her the day before she’s supposed to leave to ask what’s happening with the dog. Even then, I’d put your breakables off to the side as much as possible just in case.

Can you offer to house them in a dog friendly hotel since your floors are new and haven’t had time to unpack. Frame it as a safety issue for the dog and everybody else? Even if you’re out money, hotel overnight is cheaper than redoing new, nice floors.

At that point, perhaps your mom will reconsider (1) dogsitter (2) just driving from their place.

e.g. “Hi mom, We’re happy to help and would love to host you, but cannot host the dog too. We’re not unpacked, won’t have time to unpack by the time you visit, and the floors are brand new. While I love [the dog], the boxes would be a hazard. Could you get a different dog sitter? If not, I’ll look into a room at ___ for you guys.”

this is a great idea actually – honestly, I would much rather pay for hotel than have a doggie catastrophe! She’s a great dog, but just large and hyper and has a giant tail that THWACKS everything in sight. and I don’t even know what’s in half of the boxes at this point, because anything DH packed did not get labeled. Surprise!

I used to do all vacation planning myself, but that was typically just visiting family or friends with an occasional Vegas trip meetup with friends thrown in. My boyfriend loves to travel and has done so extensively so I’m traveling a lot more these days but planning far less. We typically pick someplace we’ve been wanting to go (we have a long list!) or the family/friend event we want to attend and then each do some research on costs, where to stay, etc. When it gets to the point of booking, he normally figures out the details and I give the final go ahead. This works for us because he has more flight preferences than I do and he knows the hotel brands that I like. We still travel mainly to visit family or friends, but normally try to tack on a trip for just us to it (we did a Seattle trip after my family Christmas last year, a weekend in Philadelphia after seeing his family, etc).

As for saving for trips, I have a separate ING/Capital One account that I add to each month. I try to guesstimate expected travel costs for the next 6 months-year and then put in a monthly amount that would total that number in time. Right now I’m putting in $275/month after completely emptying the account for the huge road trip we just took.

Perfect timing for a vacation thread. Does anyone have a recommendation for a boutique hotel in Seattle? I’m looking for something with character and/or a luxurious feel. Or should I go adventurous and try airbnb?

I love the Hilton Artic Club – It’s a technically a Double Tree I think, but it was previously a boutique hotel and has so much charm. The theme is like, pacific northwest expedition ? But all the doorknockers are walruses, and there is a stuffed walrus in every minibar. I know that’s irrelevant, but I think it’s adorable. The service is really amazing for a big chain hotel.

Inn at the Market. They have a beautiful deck with comfortable chairs and lovely flowers and the best part is that you get to loll around while looking straight out at Elliott Bay. The hotel’s location is unbeatable for restaurants and sightseeing.

The Sorrento hotel. It is older with a beautiful cozy lobby and great food in the bar and more upscale restaurant. You are close to downtown for shopping, riding the waterfront ferris wheel, Pike Place, and Capitol Hill- which has a great food and music scene.

I am in the corporate world – our company plans a trip to the Caribbean each year as an incentive for our sales team, and corporate staff get free airfare for 2 and a hotel room as well. So I count that as my annual vacation. Of course I have to work some while I’m there – but the fact that the CEO and all of the VPs are there too means they need less from me than they would if I were on vacation somewhere else and they were in the office! Besides that, I take a week to visit family in another state but plan to do some work while I’m there or else plan it as a long weekend around a holiday like Thanksgiving or Christmas (when no one is likely to need much from me).

I have a general idea of how I expect to spend but don’t have a specific budget or account. I like my vacations to be quite active, a lot of sightseeing and planned activities. My best friend is the greatest travel companion ever, she does quite a bit of research and puts together an agenda which is detailed but offers flexibility (choice of two activities or a few restaurants). My husband is the opposite, he does not like to do any planning and doesn’t mind if he ends up just relaxing and doing nothing.

I love to travel and tend to travel fairly frequently, at least every other month. These trips are usually a mix of traveling home to the Caribbean to be with family, smaller (US, mostly) trips to visit friends and longer international trips. I try to travel home at least twice a year, always at Christmas and usually in summer, too. These trips are all about family and relaxation and almost the only cost is airfare (don’t eat out much, few expensive activities, etc). I usually stay with friends/family for the smaller trips, which are mostly to major cities in the East/SE. These trips are normally less than a week and the major costs are flight and food. I tend to eat out a lot more when visiting friends.

I try to take one long (1-2 weeks) international trip every year, usually with my parents and/or siblings. My mom travels all over for business, so we often use her business trips as a springboard to visit places like China, Paris and Switzerland. I get the dual benefit of spending time with family and visiting somewhere fun. Those trips always include lots of sightseeing and trying new foods.

No matter what type of trip I take, I always make time for relaxation, even if it’s just sleeping in a few hours. Other than traveling home, I prefer to travel in the off season (spring and fall), when school is in and demand is lower. It’s usually cheaper and less crowded. I don’t have a specific travel savings account, but try to informally set save for travel and spread the cost over a few months by buying the flight in advance and purchasing groupons or similar for food, activities and hotel. I love visiting new places and experiencing different cultures, especially their art, history, food, etc.

I like the distinction between vacation and traveling. I never consider visiting family to be vacation. I love my family, but you all know what I mean. I’m glad that I have generous leave so I don’t have to use all my PTO for visiting family. We like to vacation in February/March because work is usually slower AND that’s when it’s cold and you need to go somewhere warm. I think our point of contention is that my bf is never up to “vacationing” somewhere cold and always wants to do someplace warm, whereas I think skiing or snowshoeing or going to Canada in January is fun as long as you have the right gear.

How do you go about planning vacation when you are single?
I get 20 days off after working for 5 years at my company (14 days before that) but I have no idea how to really use these extra days. It is end of August and I have only taken about 4-5 days off all year for various weddings, camping trip but no real vacation. My family stays abroad (not a very vacation/travel friendly region for women) and they visit me during Christmas/New years and mostly want to stay home, enjoy some down time, shop, dine and relax. I usually end up doing a staycation to spend time with them.

What are some good vacation spots in US for going solo where I don’t feel too awkward by myself? I want to keep it to US initially if I am traveling alone. Would like to do something relaxing, chill and not too much outdoorsy stuff (already did hiking/camping with few friends).
Most of my friends are always booked with their SO/family for vacations (which is expected) and it is so difficult to coordinate time/budget/activity/location with everyone.

I’m single. As I said above, I use part of my vacation to see my family, part to visit friends and part for new places. Can you visit your family abroad and make it more of a family trip than a travel/sightseeing trip? Can you plan solo vacations to visit friends who live in other US cities? My friends usually are usually working when I visit, so I entertain myself during the day and meet up with them in the evenings, as schedules permit.

Most major cities are solo vacation friendly. I’ve even gone to fancy restaurants by myself, both for personal and business travel. My (completely not street-smart) sister had a fabulous solo vacation in San Francisco. I’d also recommend New York, Chicago, Atlanta, Washington DC, etc. I’m an introvert, so I usually have my kindle for solo meals and transportation, but my sister the extrovert talks to people and makes new friends wherever she goes.

Honestly, planning vacations as a singleton was so, so much easier than planning as a couple or for a group! Think of it – you can do whatever you want! Fabulous.

I agree that if you aren’t used to it it can take one or two trips to get used to, but just jump in and try it. As for where to go – the simple answer is, anywhere you are interested in seeing. Just follow some basic safety precautions for women travelling alone (e.g. plan your itinerary in advance and tell people where you will be), don’t put yourself in unsafe situations (e.g. walking home alone late at night in the dark) and you will be fine. Don’t worry about it!

Sounds like the easiest thing to do to get yourself started would be to choose a city you’d like to visit – San Francisco? Boston? Chicago? Book yourself some accommodation in a central area and you are good to go. Sounds amazing to me.

Any recommendations on vacationing as single mother? Finding that to be H.A.R.D.- no one wants you to tagalong, visiting family isn’t a vacation, going with me and her solo is too hard/no break while she’s young. This weekend, paying a sitter to come along to a cabin- pricey but if it works well won’t be the last time. Going with friends didn’t work well; they wanted to be more active than we could and stayed up too late making noise.

How old is your daughter? What about a resort type place that has a kids club/babysitting option? You guys could have fun romping around/in the water, then she could get some time with other kids while you explore or just veg out at the spa. Just an idea. I can see it would be hard. I would think friends with kids the same age would be game for a group trip, but maybe that is just me.

Have you tried vacationing with just one friend, preferrably a friend who’s an “auntie” to your kid? It’s a “family-type” vacation, very different from a cabin trip with a group, but it’s fun nonetheless.

I’m looking forward to the overnight trip I’m planning with a friend and her two year old. It’s a great excuse to do all the fun kid stuff that adults don’t normally get to do without getting strange looks (build sandcastles, go on kiddie rides, sing The Itsy-Bitsy Spider, etc).

I travel primarily on my own, though I think I do it a little backwards- instead of planning ahead in the year when I’ll take a vacation (like oh, I will vacation in July), I generally just keep an eye out for cheaper flights, and then go book them, schedule allowing. I like to travel, not vacation, so that usually helps to narrow my general list of destinations, though really, I’m not super fussy, I just don’t love beach resort vacations. Once I’ve booked my flight, I find accomodations, and buy a few travel books for the locations, get travel insurance, etc., and that’s basically it. I love travelling alone, though my parents HATE that I do it, I did an exchange in Europe, and since then I’ve been back a few times, plus a few American/Canadian destinations.

I am also young enough (mid-20s), that staying in a hostel is totally okay, so sometimes I’ll do that for one or two nights, just to have the company of other young travellers, though I do tend to use airbnb a lot and rent condos/apartments, mostly because I really like having a kitchen and shopping at farmers markets in various cities.

It’s a free-for all when travelling alone. If I want to sit in a park and read all day, I do. If I want to gorge myself on local pastries while lying on my bed, I do. If I want to see all the museums, I do. If I want a fancy meal in a great restaurant, I make it happen. I’m a big planner, so I usually have a checklist of things I want to do, but really, it’s totally fine to just go and wander.

For safety, it’s really just being smart and aware. I’ve also only really done Europe and NA alone, and both are pretty safe for solo women travellers, especially if you speak the languages, so, it’s been fine so far. I’m off to Lisbon and Benelux in May for 3 weeks, and I’m so very excited.

Agreed! I have the opposite problem: I live with my SO in a city that is a plane ride away from most of my family and friends so I spend all of my vacation time visiting or traveling with them. SO recently suggested that we take a trip together because we realized we hadn’t taken a “real” vacation (>3 day weekend) together in a few years.

I think any city where there are a lot cultural things to do and it is easy to get around on public transportation would be great. NYC would be my #1 choice, but I’m biased (and don’t know where you live). Boston and Chicago would both work, too. Or Washington DC. Back in my single days, I loved going anywhere with interesting museums, theater options, great walking, and fun shopping. I like to go to dinner on my own somewhere nice, sit at the bar or bring a book. I don’t mind going to the theater or movies on my own and museums are almost better without someone else tagging along!

I know you said US, but you should go to Paris! Tons of great walking, a million museums, rent a bike in the park, picnic wherever, and then go have dinner at tiny little holes in the wall. Montreal would also be fun.

Surprisingly, I think Vegas would be a great solo vacation spot. I’ve done several trips there w/ my husband’s friends but I haven’t always wanted to do everything they were doing so I did some solo stuff. I went shopping, swimming, to some museums, did an indoor rock climbing thing, there is just SO MUCH to do there. It is also totally common for people to go there as a group but end up solo because they are the only one not hungover or the only one that is hungover and stayed back. Everyone is so interesting and there is so much people watching. Most gambling is also a solo activity if you are into that sort of thing. There are tons of great “food courts” that actually have gourmet food and buffets too so no need to sit in a regular restaurant alone if you are nervous about that.

Traveling by myself is my favorite part of being single. I’m personally partial to Paris, but europe is really easy single as is anywhere in the US. I tend to do beach vacations w single girlfriends or married girlfriends on their own. My goodness don’t wait for a partner to travel!

I went to DC in that situation. I ended up staying at a Quaker hostel, chosen because the mix of location and cost couldn’t be beat. But… I just loved it. Because it is run by the Quakers, there is no drinking, meaning that it was filled with sightseers instead of partying 19-year-olds. I was able to get some social, adult interaction every day, which made the trip much more fun. (Not sure if others have this experience, but when I travel alone I can go days without having more than a cursory interaction with someone, which can be mentally tough. What can I say, I’m a primate and therefore social.)

We did a 10-day trip to the Balkans earlier this year. We covered Slovenia (Ljubljana), Bosnia (Sarajevo and Mostar…Sarajevo was the highlight of the trip for me), and Croatia (Zagreb and Dubrovnik).

Dubrovnik was stunning but very very crowded. The food in the Old City was mediocre at best…our favorite place was a restaurant called Otto Taverna near the Port (try the rump steak…it’s TDF!). If you have time, I’d recommend a day trip to Mostar. Charming old town with lots of interesting Ottoman style buildings (and visible scars from the war). The highlight was the famous Old Bridge (you can get an amazing view from climbing the minaret of one of the mosques nearby).

Zagreb reminded me a lot of Vienna. Very beautiful Austro-Hungarian style architecture. Great restaurants, cheap wine, friendly people…I had a great time there.

My parents retired to a beach town, and live in a house that can accommodate guests. It’s a great way to have a trip/vacation with kids since the adults outnumber the kids (my parents are relatively young and help a ton with the kids).

We do days at the beach, boating, the cheesy amusement park at the boardwalk, outlet malls, the pick-your-own peach orchard, you name it. We’ve usually hired a local babysitter for a night or two of non-kid dining (either a local high school student or a college student).*

The drawbacks: my dad is not a kid person, we have to hammer out an Annual Trilateral Agreement Not to Talk Politics or Watch Cable News, the drive from the airport to their house is long, and humidity.

The kids are now 5 and 2, and it gets easier every year to travel with them. I swear I could probably put the 5 year old next to any adult who could use an iDevice and she’d be fine.

I’d love to try Hawaii sometime, but maybe in a few years.

*These are usually family friends/acquaintances, but I’ve actually hired a babysitter through a hotel concierge a couple of times. It worked out fine, though hotels are hardly the most fun places for little kids, apart from the long halls.

I love to travel. We try to go on one “go somewhere new” every year. I hope to continue that until I’m too old to move.

In terms of tips, I like to go right on the “shoulder” of peak tourist season so everything is still open, weather is still good, but you’re getting a better deal and not dealing with very large crowds. A lot of time that equals traveling in September/October. If I can help it, I also like to get in as early as possible on the day I come back so that I have most of that day to get back in the swing of things before I have to go back to work. If I can get a day between vacation and work, even better. For planning, we just pick a place, book tickets and then work backwards to figure out everything else. Sometimes we just look to see where tickets are cheap and go there. I tend to do a healthy amount of research, but I don’t like to plan the day to day because I don’t want to have that much structure. With my SO, I do almost all the planning and he just chimes in with any “musts” and figuring out maps (for hotels, etc.). I wish he did more of the planning but I would probably then just complain that he didn’t do something right so I let that one go.

We didn’t do it the last two years but we used to go to Florida every winter for just a long weekend/3-4 days. If you time it right, it can be a very inexpensive trip from NY and it’s a great way to recharge in the winter. I always felt like I would look forward to it and then feel like I could deal with February because I defrosted. I think we’re going to try for that again this winter.

My staycations usually don’t turn out to be productive but I do love being home when everyone else leaves (like for Memorial Day or Labor Day) because I feel like I get to have NY to myself and can just go to brunch with no lines, etc.

Seriously. The best quote on EaterSF this week went something like this: “Ah, it’s that time of year again . . . when half the city can’t wait to head out to Burning Man and the other half can’t wait for them to leave.”

If you’re staying for 4+ days, it’s cheaper (& more fun) to rent an apartment than stay in a hotel. Lots of good websites for this, like vbro.com & rentparis.com. You can shop for breakfast & lunch foods at the outdoor markets, boulangeries, chartucharies, cheese shops, etc., & eat very very well.

Look online for Metro passes — again, depends on how long you’re staying if they’re worth the cost & on if you prefer walking miles or not. You’ll walk a lot no matter what, but some museums & sites can be distant. Same goes for museum passes — if you’re a museum junkie & staying for a week, the pass can save money & time (bec. you don’t have to stand in line & places like the Louve ALWAYS have long lines).

Paris is very expensive, even more so than NYC or London, but worth it.

I try to take two big international trips per year since I get 3 weeks’ vacation per year and try to maximize it by tagging my vacations onto days we get already off (e.g., I’m leaving tomorrow to go to Peru to maximize the Labor Day holiday and then I’ll be going to Africa over Christmas and New Year’s so I only have to miss 6 days of work for an 18 day vacation).

I’m single and typically join an age-appropriate tour group, although last year my mom and I did Eastern Europe together on our own. This way I get to see some far-flung places without having to do a lot of planning (other than booking the tour and the airfare), feel safe while doing it and meet new people. It also helps with budgeting — with most of the tours you get a pretty good idea of what everything will cost, so if I figure out all my trips at the beginning of the year I know exactly how much I’ll need for both, especially since I don’t usually buy a lot when I travel.

For a while I hated that I never had someone to travel with. There are a lot of places that I’d feel comfortable going without a tour (like most of Europe), but I just don’t enjoy spending 10 days by myself, eating every meal alone. So rather than feeling sorry for myself that I don’t have a travel partner (especially since my ex and I were supposed to be going to Scotland tomorrow), instead I pick crazy places to go that I wouldn’t consider without a tour group. Like Africa. And I have to say, I am so so so much more excited about going on safari and seeing mountain gorillas in the wild or taking a canoe into the Amazon jungle rather than just seeing some old castles in Europe.

I’m doing Peru solo myself this fall, but I’m thinking I might use a tour group for Africa, which is next year (if financially feasible!). Can you let us know what your thoughts are on those tour companies? Have fun in Peru!

I’m very aware of that and I don’t believe I ever referred to it as a country…Besides, I fail to see the problem with stating that I’m going to Africa as a place/destination, particularly since I’m going to multiple countries within Africa. I also referred to going to Europe as a destination, but that didn’t seem to warrant a rant…

My husband & I are travel junkies & plan at least 2 trips a year, spring & fall. I just put them on my work calendar & schedule things around it — plan it far enough in advance (at least 6 months, if not longer), & nobody else in the office has a legit reason to complain.

Likewise, planning far in advance means we can save up if we want to do something wild, like cruise the Antarctica peninsula or rent a chateau in the South of France with 8 friends (that’s the kind of stuff we love to do). Work to live, not the other way around!

I take tons of vacation. I use all of my vacation (4 weeks), and have taken off time this year (extra 2 weeks) that was not “counted” towards my vacation, per partner request (i.e., I met my billing hour quota <8 months into the fiscal year, and the partners I worked for probably thought I was going to quit). I am not married, but in a long-term relationship and am childfree. Because my boyfriend is on a drastically different budget than I am, so we do one big vacation and one small vacation together a year, and I do one on my own or with friends. I actually like traveling on my own, particularly in foreign countries, as it lets me do what I want (see what I want, go to famous restaurants, beach, go on nature adventures, etc.).

I've also worked in another sort of "vacation." I just cannot handle the weather where I live very well. So when I get depressed because of the weather, I go back home to the OC, and will work from there for weeks at a time, particularly as I have become more senior. Because I am staffed between two offices, forward calls to my mobile, work from home a good deal anyways, and bill plenty hours, I am not sure if anyone even notices unless I tell them. Managed a massive summary judgment filing from a lounge chair by the pool once – I view it as one of my greatest professional accomplishments. ;)

I don’t do a lot of upfront budgeting for our holidays but have found that recording and reviewing discretionary costs afterwards is a good discipline for planning/ prioritizing future trips (‘oh I see that the restaurants we liked best were all around x euros per head – more of those and less of the others next time’). I usually need a record anyway, to cross check against credit card statements, but it is useful to have the info in one place and which can be looked up a few years/ trips later.